Novel gallium-mediated C3-allylation of indoles and pyrroles in aqueous media promoted by Bu4NBr

A mild and efficient protocol for the coupling of indoles and pyrroles with allyl halides such as allyl bromide, crotyl bromide and propargyl bromide in the presence of gallium metal in a Bu4NBr-DMF-H2O system has been developed. The reaction is equally effective when cadmium is used in lieu of gallium and the corresponding 3-allyl indoles and 3-allyl pyrroles were obtained in almost comparable yields. (c) 2006 Elsevier Ltd. All rights reserved.